WO2008139894A1 - Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same - Google Patents

Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same Download PDF

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Publication number
WO2008139894A1
WO2008139894A1 PCT/JP2008/058081 JP2008058081W WO2008139894A1 WO 2008139894 A1 WO2008139894 A1 WO 2008139894A1 JP 2008058081 W JP2008058081 W JP 2008058081W WO 2008139894 A1 WO2008139894 A1 WO 2008139894A1
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WO
WIPO (PCT)
Prior art keywords
group
disease
membered ring
same
formula
Prior art date
Application number
PCT/JP2008/058081
Other languages
French (fr)
Japanese (ja)
Inventor
Naohiro Takemoto
Kenji Murata
Norihito Murayama
Chikaomi Yamada
Original Assignee
Asubio Pharma Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to ES08764246T priority Critical patent/ES2453590T3/en
Priority to CN200880021294A priority patent/CN101730691A/en
Application filed by Asubio Pharma Co., Ltd. filed Critical Asubio Pharma Co., Ltd.
Priority to PL08764246T priority patent/PL2151439T3/en
Priority to BRPI0810821A priority patent/BRPI0810821A8/en
Priority to US12/596,054 priority patent/US8592435B2/en
Priority to KR1020097024649A priority patent/KR101456316B1/en
Priority to DK08764246T priority patent/DK2151439T3/en
Priority to MX2009011369A priority patent/MX2009011369A/en
Priority to SI200831176T priority patent/SI2151439T1/en
Priority to JP2009514083A priority patent/JP5197584B2/en
Priority to RU2009143850/04A priority patent/RU2470927C2/en
Priority to EP20080764246 priority patent/EP2151439B1/en
Priority to CA 2683941 priority patent/CA2683941C/en
Priority to AU2008249329A priority patent/AU2008249329C1/en
Publication of WO2008139894A1 publication Critical patent/WO2008139894A1/en
Priority to US13/482,375 priority patent/US8685989B2/en
Priority to US14/173,327 priority patent/US9139559B2/en
Priority to HRP20140326AT priority patent/HRP20140326T1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/30—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom
    • C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D241/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

Abstract

Disclosed is a compound which has both of a neurite elongation activity and an angiogenesis enhancement activity, and which is applicable to the amelioration of a disease including a head injury or a central nervous system injury (e.g., spinal cord injury), cerebral infarction, an ischemic heart disease (e.g., cardiac infarction, organic angina) and a peripheral arterial disease (e.g., critical limb ischemia), or a sequela of the disease. Specifically disclosed is a compound represented by the formula (I). Preferably, in the formula (I), the group Nx represents an aromatic 6-membered ring having two nitrogen atoms; R0, R1 and R2 independently represent a hydrogen atom, an alkyl group, an amino group or the like; E represents an oxygen atom or a group -NR8 [wherein R8 represents an alkyl group or the like]; n represents an integer of 0 to 5; X and Y independently represent a bond, a cycloalkyl group, -CO- or the like; and Q represents a hydrogen atom or a phenyl group.
PCT/JP2008/058081 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same WO2008139894A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
CA 2683941 CA2683941C (en) 2007-04-27 2008-04-25 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
MX2009011369A MX2009011369A (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same.
PL08764246T PL2151439T3 (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same
BRPI0810821A BRPI0810821A8 (en) 2007-04-27 2008-04-25 DERIVATIVES OF SIX MEMBER AROMATIC RINGS CONTAINING NITROGEN AND PHARMACEUTICAL PRODUCTS CONTAINING THE SAME
US12/596,054 US8592435B2 (en) 2007-04-27 2008-04-25 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
KR1020097024649A KR101456316B1 (en) 2007-04-27 2008-04-25 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
DK08764246T DK2151439T3 (en) 2007-04-27 2008-04-25 Nitrogenated AROMATIC 6-membered RINGDERIVAT, AND THIS pharmaceutical composition comprising
ES08764246T ES2453590T3 (en) 2007-04-27 2008-04-25 6-membered nitrogenous aromatic ring derivative and pharmaceutical agent comprising the same
SI200831176T SI2151439T1 (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same
RU2009143850/04A RU2470927C2 (en) 2007-04-27 2008-04-25 Derivatives with nitrogen-containing six-member aromatic ring and pharmaceutical products containing said derivatives
JP2009514083A JP5197584B2 (en) 2007-04-27 2008-04-25 Nitrogen-containing aromatic 6-membered ring derivatives and pharmaceuticals containing them
EP20080764246 EP2151439B1 (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same
CN200880021294A CN101730691A (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same
AU2008249329A AU2008249329C1 (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same
US13/482,375 US8685989B2 (en) 2007-04-27 2012-05-29 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
US14/173,327 US9139559B2 (en) 2007-04-27 2014-02-05 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
HRP20140326AT HRP20140326T1 (en) 2007-04-27 2014-04-04 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007118768 2007-04-27
JP2007-118768 2007-04-27

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/596,054 A-371-Of-International US8592435B2 (en) 2007-04-27 2008-04-25 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same
US13/482,375 Division US8685989B2 (en) 2007-04-27 2012-05-29 Nitrogen-containing six-membered aromatic ring derivatives and pharmaceutical products containing the same

Publications (1)

Publication Number Publication Date
WO2008139894A1 true WO2008139894A1 (en) 2008-11-20

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ID=40002110

Family Applications (1)

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PCT/JP2008/058081 WO2008139894A1 (en) 2007-04-27 2008-04-25 Nitrogenated aromatic 6-membered ring derivative, and pharmaceutical agent comprising the same

Country Status (18)

Country Link
US (4) US8592435B2 (en)
EP (2) EP2151439B1 (en)
JP (1) JP5197584B2 (en)
KR (1) KR101456316B1 (en)
CN (2) CN103396399B (en)
AU (1) AU2008249329C1 (en)
BR (1) BRPI0810821A8 (en)
CA (1) CA2683941C (en)
CY (1) CY1115377T1 (en)
DK (1) DK2151439T3 (en)
ES (2) ES2566327T3 (en)
HR (1) HRP20140326T1 (en)
MX (1) MX2009011369A (en)
PL (1) PL2151439T3 (en)
PT (1) PT2151439E (en)
RU (1) RU2470927C2 (en)
SI (1) SI2151439T1 (en)
WO (1) WO2008139894A1 (en)

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EP2462133A1 (en) * 2009-08-07 2012-06-13 Dow AgroSciences LLC 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives
JP2013501724A (en) * 2009-08-07 2013-01-17 ダウ アグロサイエンシィズ エルエルシー 5-Fluoropyrimidinone derivatives
WO2016047662A1 (en) * 2014-09-25 2016-03-31 第一三共株式会社 Therapeutic agent for cerebral stroke
US9840475B2 (en) 2012-12-28 2017-12-12 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9908855B2 (en) 2012-12-28 2018-03-06 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives

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AU2013370494B2 (en) 2012-12-31 2017-08-17 Adama Makhteshim Ltd. 3-alkyl-5-fluoro-4-substituted-imino-3,4-dihydropyrimidin-2(1H)-one derivatives as fungicides
WO2016086105A1 (en) * 2014-11-25 2016-06-02 Shriners Hospitals For Children MODEL SYSTEMS FOR SCREENING MODULATORS OF mTOR SIGNALING
CN114570418B (en) * 2022-02-22 2023-10-17 陕西延长石油（集团）有限责任公司 Catalyst for preparing methyl sarcosinate from methyl glycolate and sarcosine, and preparation method and application thereof

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Cited By (7)

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EP2462133A4 (en) * 2009-08-07 2013-01-16 Dow Agrosciences Llc 5-fluoro-2-oxopyrimidine- 1(2h)-carboxylate derivatives
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US9840475B2 (en) 2012-12-28 2017-12-12 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxamide derivatives
US9908855B2 (en) 2012-12-28 2018-03-06 Adama Makhteshim Ltd. N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives
WO2016047662A1 (en) * 2014-09-25 2016-03-31 第一三共株式会社 Therapeutic agent for cerebral stroke

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